


Pretty Messed Up Situation

by SurlyCat



Series: Porny Presents [2]
Category: Supernatural
Genre: Alternate Universe - Modern Setting, Anal Plug, Anal Sex, Bottom Dean, Discipline, Dom/sub, Dominant Castiel, Episode: s04e17 It's a Terrible Life, Fluff and Smut, M/M, Office Sex, Secretary Castiel, Sub Dean, Top Castiel
Language: English
Status: Completed
Published: 2014-10-06
Updated: 2014-10-06
Packaged: 2018-02-20 05:05:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,501
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2415986
Author URL: https://archiveofourown.org/users/SurlyCat/pseuds/SurlyCat
Summary: <blockquote class="userstuff">
              <p>Eyeing the clock at the corner of the computer screen, Dean's palms begin to sweat. Castiel would be there within the next five minutes to start their workday, and Dean had been bad. After all, your Dom tells you to wear the pink satiny panties he found in your dresser, you freakin' wear them; you don't show up in your boxers just because you feel like your ass looks too big. Normally they don't risk playing during business hours, but Dean has a feeling that today will be one of those rare exceptions.</p>
            </blockquote>





	Pretty Messed Up Situation

**Author's Note:**

  * For [i_know_angel](https://archiveofourown.org/users/i_know_angel/gifts).



> This...ended up being about twice as long as I intended. But I was having feelings, and that's really my only excuse. So yeah, this is what happens when my friend gives me Dom!Cas and sub!Dean feelings in the middle of the afternoon and then I have to stew over it for days without an opportunity to get anything down. Barely edited, so apologies for any glaring mistakes.

Eyeing the clock at the corner of the computer screen, Dean's palms begin to sweat. Castiel would be there within the next five minutes to start their workday, and Dean had been bad. After all, your Dom tells you to wear the pink satiny panties he found in your dresser, you freakin' wear them; you don't show up in your boxers just because you feel like your ass looks too big. Normally they don't risk playing during business hours, but Dean has a feeling that today will be one of those rare exceptions.

Three minutes. Maybe Cas will have forgotten about the order he gave before he left Dean's apartment the night before. Dean rolls his eyes at himself because there's pretty much no chance of that happening. It's one of the reasons Cas lasted beyond the probationary period and officially secured the position as Dean's secretary; the man has an ungodly memory, impeccable sense of organization and time management, and intuits Dean's needs nine times out of ten.

At exactly eight o'clock comes the knock at his office door, and Dean straightens up in his seat, willing his face into his standard 'I'm a fucking professional' expression that he carries at work.

"Come in," he calls, fixing his eyes to the spreadsheet on his screen.

"Good Morning Mr. Smith," Castiel greets as he steps through the door. He uses an elbow to close the door behind himself while his hands are full with Dean's breakfast in one hand, and his own coffee in the other.

Dean doesn't quite understand why Cas insists on calling him Mr. Smith whether anyone's there to hear it or not, but he can't deny that he kind of enjoys it. Especially on the rare occasion that Cas decides to call him that when business hours are over; it comes dangerously close to a teacher kink of his, but Dean keeps that to himself. Liking getting spanked over your desk or begging for your secretary's cock while kneeling at his feet are kinky enough, and he doesn't need to give Cas any more ideas.

"Did you wear them?" Cas asks quietly, eyebrow cocked as he sets Dean's bowl of honeydew and cantaloupe down on the desk.

"No," Dean murmurs, his face heating. He can't even bring himself to look up from Cas' hand where it's paused, resting on top of the clamshell container.

"And why not?" Cas asks, voice calm and serious.

He finally looks up and considers giving some bullshit about forgetting, but Cas will know if he's lying, and he's already in it deep enough.

"I don't think they're very um…flattering on me anymore, Sir," he says carefully, hoping to soften the blow of what he's really saying. He knows now not to say anything directly negative about his body around Cas anymore.

Cas sighs, and his eyes are so damned disappointed that it may as well be a punishment in itself. But then they level back out into their typical cool look, and he squares his shoulders.

"Mr. Smith, it is not up to you to determine whether I find something pleasing or not. My order was an _order_ , not a suggestion, and you know I can't let that go," Cas says, voice low and firm.

"Yes, Sir," Dean nods, feeling the flush reach his ears now. Of course Cas just had to go and use the moniker just then.

Cas takes a sip of his coffee, keeping a careful eye on Dean over the lid of his cup. Dean knows that the pause is his way of giving Dean the chance to object to taking his punishment during work; Cas made it clear early on in this thing of theirs, that he doesn't want to sabotage Dean's career. But maybe Dean's feeling a little more masochistic than usual today, because he simply pushes his lips together and remains quiet, looking Cas steadily in the eye. He knows that Cas got the message when the man gives a thoughtful hum and nods slightly to himself.

"The purple plug is still in your desk, isn't it?" he asks. At Dean's nod, Cas continues. "You have thirty minutes between your 11:00 conference call and your web conference with the Stanton account today. I expect you to use the time to finger yourself open, and when you're done, you'll insert the plug. Understood?"

Dean lets out a shuddering breath through his nose. "Yes, Sir, understood."

"Good," Cas says with a nod. And then he's sliding right back into secretary mode, as if he didn't just tell Dean to shove a plug up his ass in the middle of the day. After a few minutes of reminding Dean to sign this and call there, Cas exits Dean's office with his usual polite nod.

The next three hours zip by in a blur of callbacks, signing approvals, and eyeballing spreadsheets in preparation for the conference call. Every now and then he remembers what lies ahead, but he stays busy enough that the usual anticipation that would be building by this point is merely an itchy thought in the back of his mind. Ten minutes before the end of the conference call however, the itch flares like a mosquito bite to the wrist, when he gets a popup alert on his screen to "Prepare for the web meeting". Dean can almost imagine the satisfied smirk that must have graced Cas' lips when he set up the no doubt deliberately worded reminder in Dean's calendar that morning. What a turd.

As soon as the call is over, Dean pockets the little bottle of lube he keeps in the desk, stuffs the plug in his interior suit jacket pocket, and heads out for one of the lesser-used restrooms. The walk isn't all that far, but with every step, he feels paranoid that someone will bump into him and feel the obvious shape of the plug in his jacket, or see the outline of the lube bottle in his pants pocket that's practically burning a hole against his leg. Just the thought of knowing what's about to happen has him starting to harden, and it's only by some miracle that he manages to duck into the restroom before it becomes too conspicuous.

Dean works himself open perfunctorily, deliberately blanking his mind of what he's doing and why, and it seems to work toward willing his erection away, thank goodness. It also helps that he's still somewhat looser than normal from the activities the night before, so he's able to work up to two fingers relatively efficiently. While that should have been a comforting thought, all it seems to do is dredge up the mental image of the night before, with Cas throwing Dean's legs over his shoulders and pounding into him, muscles rippling and shining with a fine sheen of sweat from exertion.

Without thinking about it, Dean works in a third finger and nearly mewls at the combined sting and familiar anticipation of knowing that soon he'd have more than just fingers. _Wait, no, dammit._ He immediately pauses his movements and simply breathes for a minute, willing himself to think about the errands he needs to do after work; anything to clear his mind of sexy thoughts. When he has himself under control, he finishes up just enough to fit the plug in, and pulls it out of his pocket. It isn't until he's drizzling lube over it that he realizes what Cas' plan must be and nearly drops the thing, catching it in midair after it slips like a fish through his hands.

This is the plug with the cordless remote controlled vibe.

And the controller is most certainly in Cas' desk.

Dean's hands shake in a dizzying combination of aroused anticipation and nervousness, but he finally manages to get the plug in and grimaces as he straightens back up to get his clothes back in order. He wore the mint green shirt and slightly darker green tie, and charcoal suit with matching suspenders that Cas seems to like so much, as a sort of unspoken pre-emptive apology for his neglect in wearing the panties. Now though, he wonders if that was a mistake, because it could very well look like he wore it as a taunt. Sighing, Dean exits the stall and washes up, counting his blessings that no one came into the restroom.

The walk back to his office is nerve-wracking, as he tries to measure his steps to look as normal as possible while feeling the plug jostling against his inner walls. There's nothing he can do about the blush rising on his cheeks as his thoughts inevitably turn to Cas now, but at least he had the foresight to drape his jacket over his arm to conceal the rapidly growing erection in his pants.

He manages to make it without any apparent suspicion, and heaves a sigh of relief as he closes the door to his office behind him. Dean isn't surprised to see Cas sitting in the guest chair at Dean's desk, tapping away at his phone. A chime sounds from it that Dean knows to be the sound of an email being sent, and then Cas pockets his phone and stands up. Without having to be asked, Dean turns his back to Cas, and seconds later feels a hand prodding at his ass, feeling for the shape of the plug between his cheeks. Seeming satisfied, he nudges at Dean's shoulder to turn back around.

"Have a seat," Cas orders, then sits back down in his own.

Before he can even make it all the way around the desk, Dean is hit with a jolt that makes him yelp as the vibrations start up in his ass, and he has to clasp the edge of the desk to keep from stumbling. He whips his head over to look at Cas, and the man definitely has a smirk tugging at his lips.

"I thought you could use a couple of minutes to get used to the sensation before starting up the meeting," Cas says innocently. "And don't worry, no one should be able to hear it; the cushion of your seat should muffle it well enough."

Dean barely holds back a glare, opting instead to focus on- gingerly- sitting down. The pressure of sitting makes him feel fuller, but thankfully, seems to dampen the vibration a bit. He's grateful for the distraction of getting logged into the meeting site, and after a moment, starts to think that maybe, just maybe, he'll survive. Despite the fact that his web cam will be on, there are about eight other people attending, and he doesn't have to give a presentation, so at least the focus won't be on him too much.

Right after the little 'ding' sounds to let him know that the meeting is beginning, the vibe cranks up another notch, and a high-pitched sort of grunt sounds in his throat.

"You're doing good, Dean, but now it's time to focus. Turn on your webcam," Cas says calmly.

Dean directs a string of unkind and petulant thoughts Cas' way, but turns on the camera anyway. His own flushed, tense face peers back at him on the screen from the little box in the bottom left corner, and anxiety fizzes inside him because there's no way he's going to pull this off. He looks up pleadingly at Cas, but the man merely frowns.

"You can do this, Dean. My third day here, I watched you give a contract-winning presentation in the middle of battling the flu. Not that I approve of pushing your body that particular way, but it speaks volumes of what you're capable of," Cas says kindly.

Cas' words bolster him more than he cares to think about, and Dean takes a deep breath before clicking the 'Join Meeting' button. Within seconds, he's plastering on his Dean Smith, Director of Marketing and Sales Smile™, and greeting the other attendees whose faces are already showing up on-screen.

Mercifully, Cas leaves the setting alone for the first few minutes while greetings are made by the other meeting attendees, and the on-screen PowerPoint starts up. Honestly, Dean doesn't really need to be present for this; the Stanton account has pretty much been sealed, and now it's mostly down to the detailed haggling over contract terms, which isn't really Dean's job. All the same though, as the face of Sales at Sandover, he's expected to make an appearance just in case something goes down and he needs to step in and salvage the situation. And part of making an appearance is pretending to be interested and nodding and laughing at all the right times, no matter how shitty the little jokes are that Mr.-

The vibe cranks up a notch, and a combination gasp/whimper punches out of him that has him rushing to play it off as a cough when four different faces look back at him on the screen. He gives a hoarse 'excuse me, sorry', and a little wave, and a moment later they all go back to the topic at hand.

A piece of paper slips across his desk, a note written in Cas' neat scrawl.

_You need to focus, Dean. Stanton is important._

Dean darts his eyes up, barely holding back a glare, more for the sake of the camera than anything, and glues his eyes to the screen. He makes an honest effort to get his brain back onto the topic of the meeting, despite how difficult it is with the plug starting to pulse the vibrations; oh god, he regrets finding the stupidly fancy thing. And he's feeling pretty proud of his ability to ignore it, until Cas stands up and comes to stand to the side of the desk, just out of line of the camera, and leans against the solid oak bookcase three feet away from the desk. Dean would have to actually turn his head to be able to see Cas in more than his peripheral, but for obvious reasons he can't just go craning his neck around so he tries his best to ignore the man.

A soft sigh escapes Cas' nose, and Dean flicks his eyes over just enough to see that Cas is leisurely palming himself over his slacks, fully erect, and eyes boring right into Dean. Swallowing harshly, Dean forces his eyes to look back to the screen, but it's not entirely voluntary, the way his ass grinds back a little bit in his seat, seeking more sensation than he's already getting. The action pushes the plug in a very satisfying way, but he dutifully swallows back a sound and merely lets out a deep breath through his nose.

 _"You alright there, Smith? You're not looking so hot,"_ Bob something-or-other asks suddenly.

Dean glances at his own little square of screen, where he can see himself looking far too flushed and a thin sheen of sweat on his forehead. Shit.

"I'm fine. Think I may have had some bad sushi," Dean fibs. "Carry on," he says with a dismissive little wave.

 _"Well, we're almost done here, if you can just make it a few more minutes,"_ Bob says sympathetically, and Dean nods back with a thin smile.

Cas lets out a barely audible but dark chuckle next to him, and Dean hears the man lowering his zipper. He can feel his face flushing hotter as a quiet hiss sounds next to him, and he can see Cas pull himself out and start stroking in peripheral. Goddammit he wants to look. Dean wants to look and beg to be allowed to touch Cas' cock, but there's no way that's happening, and it's _horrible_. Seconds later, the vibe clicks down to its lowest setting, and at first it's a relief. At least he's able to form together some sort of response when asked a question and even throw in an opinion when the topic of the meeting comes closer to his area of expertise.

Cas finally moves, and comes to stand right in Dean's line of sight on the other side of the desk, and speeds his strokes, his breath making these little hitching noises that Dean knows to mean that Cas is about halfway there, when they have to be quiet. He can't help but shift his hips slightly, needing something, anything, because the vibe is just low enough now to keep him on a steady plane of arousal; completely aware and unable to ignore it, but not enough to tip him over. Dean doesn't dare touch his own dick, regardless of how it's nearly painfully hard now, but maybe the shifting will get him at least a little bit of friction against his pants, some relief. He doesn't want to come, but his body is unbearably restless and screaming at him to do _something_.

The vibe cranks up suddenly, and Dean can't help the low groan that sounds in his throat, or the blurt of pre-come that oozes out and immediately dampens his underwear. A few sets of eyes dart his way on-screen, but he just shakes his head and holds up a hand in a 'don't mind me sort of gesture' that has people giving him mixed looks of concern, disgust, and a couple just shrug and go back to what they were doing. As soon as the attention is off of him, he glances up to Cas, who now has the other hand tugging at his balls in addition to the one jerking at his cock, and Dean is struck with a deep disappointment that he won't be the one to bring Cas to his orgasm. The way the man is leaking and his eyes are half-lidded now, there's no way he's going to last long enough for Dean to finish him off.

But then those eyes focus right on him, and Cas slows his pace. "Good boy," Cas mouths, face full of pride and so fucking genuine that Dean feels his chest expand with an embarrassing amount of emotion. Dean has to take a deep breath and release it slowly, because there's no way he can let himself get carried away into emotional territory right now.

After a few more minutes of the typical summary and last minute questions, the web meeting is finally drawing to a close. He listens carefully to make sure he didn't miss anything important in all his distraction- he didn't- and it helps, to distract from the thoughts that make him feel too vulnerable.

As soon as the meeting ends and he's exited the application, Dean double-checks that the camera is off, and then leans back in his seat with a heavy exhalation and closes his eyes. He hears Cas move closer to him, and then there are gentle fingers tracing behind his ear and down his neck before sliding around to put his palm squarely on the side of Dean's neck.

"I'm so proud of you, Dean. I knew you could do it, and no one was even the wiser," Cas murmurs.

Dean opens his eyes to look up into those blues that although still dark with arousal, are tinted with warmth.

"Thank you, Ca-Sir," he says, hoping Cas didn't notice the near slip-up.

Cas brushes his thumb over the sharp line of Dean's jaw and gives him a small smile, the scent of those sanitizing hand wipes that Cas likes to use making its way to Dean's nose.

"Look at my cock, Dean," he says, voice low and smooth.

Dean looks down, and sure enough, Cas is completely hard and a pearl of pre-come is beaded at the head. It takes a moment for Dean to realize that Cas hasn't touched himself in at least a few minutes, and that he isn't sure when Cas wiped his hands, but it's been long enough that the hand touching his face is completely dry.

"You see how hard I still am? This is what you do to me, and you're not even naked; it's just you. So you can surely imagine my disappointment in hearing that you think I wouldn't desire you in the very item that I wanted you to wear," Cas chides softly, turning the vibrator down in increments as he speaks, until it's completely off. "Do you trust me, Dean?"

Dean is caught between wanting to preen at the fact that Cas is confessing how badly he wants Dean, and feeling a deep guilt at disappointing Cas. And how on earth could the man possibly ask if Dean trusts him, after all the shit he's let Cas do the past six months?

"Of course I do," Dean replies earnestly.

Cas nods and then looks down at his own cock for a moment before bringing his eyes back to Dean. "Then I need you to trust that I'm not in the business of trying to make you feel worse about yourself. You are remarkable no matter what you are or are not wearing, and nothing you can say will change my mind on that."

Dean shivers involuntarily at the sincere tone and words. The urge to point out every single flaw and argue builds in Dean's throat like acid, and he barely chokes it back. Cas' words are just as much like blows as any spanking Dean has received from the man, and he has the sense that just like a spanking, if Cas keeps going it's going to end in tears. And because Cas is Cas and can read Dean like a goddamned book, he knows that he's pushed enough for now and lets out a sigh.

"Now," Cas says, tone back to its normal authority. "Pants and underwear down, and bend over the desk."

The order is a relief within itself, and Dean rushes to comply, clearing a space on the desk and nearly dropping the lube as he fumbles it out of his pants pocket to hand it over. He doesn't want to think about Cas' words anymore, because that means thinking about the fact that this thing between them has been getting more and more personal as time has gone on, and that there have been numerous occasions recently where Dean's nearly called him Cas instead of Sir. No, Dean just wants to feel Cas' soft hands gripping at his hips and that perfect cock in his ass; he needs the distraction of sensation. _And you, know, the fucked-up way that it makes you feel needed and all that affirmation,_ Dean's brain unhelpfully supplies.

Blanking out thoughts of anything beyond getting physical relief, Dean pushes down his pants and boxers and bends over the desk, presenting himself. Cas' hand is warm where it caresses over Dean's ass, then scoots over to carefully pull the plug out. Normally there'd be some teasing, but Cas seems to have considered the time-sensitive nature of fucking in the middle of the day and no doubt even knows down to the minute how long they can spend on this before Dean's next event in the schedule. It's only because of this that Dean isn't panicking at the thought of what they're doing, because he knows he can trust Cas to have the details squared away to keep them under the radar.

Dean squirms a little at the sensation of the cold lube as Cas prods at his hole, making sure there's enough there. Cas uses his other hand to rub apologetically at Dean's hip, working two and then three fingers into him, and scissoring for a minute because Cas is a little bigger around than the plug. Dean doesn't want the careful treatment right now though, he wants all those feelings fucked right out of him, so he pushes back on Cas' fingers in a silent request to get a move on. It earns him a sharp smack to his ass that has him biting harshly on his lip to stifle a cry, and his cock pulsing harshly.

"Don't even think about trying it again, or you won't have my cock at all," Cas warns, when Dean's hips twitch back slightly.

Stilling, Dean lets Cas stretch him until he's satisfied, because he has absolutely no doubt that Cas means it. After a minute, the fingers retreat and then the head of Cas' dick is at his entrance, wonderfully warm and so smooth. Wait-

Dean looks over his shoulder, and Cas is looking at him, eyebrow cocked. Alright then, apparently Cas _didn't_ forget the condom; normally they only bareback at the end of a day or on the odd weekend scene. Just the thought of walking around for the rest of the day with Cas' come inside him and leaking out like territory fucking _marked_ has Dean whimpering in his throat as he rests his forehead back on the desk. Cas hums a satisfied sound and pushes in, agonizingly slowly; far slower than is really necessary, considering how stretched Dean is at the moment.

Thankfully though, Cas doesn't waste too long on making sure Dean is adjusted- which he is- and within seconds of bottoming out, grinds his hips against Dean's. With a grateful sigh, Dean pushes back to show his enthusiasm. Cas takes it for what it is and starts a steady pace, drawing most of the way out and then plunging in deep, hands gripping at Dean's hips. After a minute, Dean shifts a little bit, trying to relieve the uncomfortable pressure on his dick where it's trapped between his belly and the desk, and oh- OH- that's much better.

"Fuck," Dean hisses, trying to keep his voice down. But then Cas manages to hit his prostate dead-on, and he can't help the groan that starts to come out. Before it can build in volume, Cas' right hand is clamped over his mouth, and the man's pace picks up, though he seems to be avoiding hitting that spot.

"No one else gets your noises, Dean. Those are mine," Cas says, more breath than voice.

With Cas' hand still muffling him, Dean lets himself really moan at that because holy shit, Cas has never really played up the ownership thing before, and pitifully, Dean fucking loves it. The moan seems to spur Cas on, and the next thing Dean knows, Cas is draping himself over his back, and the man's left hand has latched onto Dean's where it's scrabbling for purchase on the desk. It only seems natural to spread his fingers and make room for Cas' to twine between them, even though Dean is dimly aware that that sort of familiarity is something they've never done. But it makes Dean feel good and safe, so he doesn't dwell on it. And really, it's hard to dwell on any one thought besides how quickly he can feel his orgasm building after nearly an hour of stimulation and the way Cas has started with the short quick thrusts that mean he's nearing the end as well.

"Scoot away from the desk a little," Cas grunts, only barely pausing for Dean to comply. "Can you stay quiet if I move my hand?"

As much as he wishes he could say yes, Dean knows by the graze of Cas' dick against his prostate again with this modified angle, that he won't be able to do it when Cas start really going at it again. Dean shakes his head no, and Cas lets out a breathy but not unkind chuckle.

"Touch yourself, Dean," he orders.

That's a fantastic idea, so Dean reaches between his legs and groans when his hand wraps around his long-neglected cock, grateful for the hand covering his mouth. Cas fucks into him as hard as he can with the loss of leverage, hitting that spot over and over and curiously, it isn't the way he's jerking his cock or the stimulation to a bundle of nerves, or even the permission to come, but something much more subtle that does Dean in.

It's when Cas buries his face in the back of Dean's neck and says "Come for me, Dean," and Dean feels Cas' fingers tighten around his own.

There have been plenty of times that Cas has ordered him to come, and it's always a good trigger for an orgasm, but that hand squeeze combined with feeling so completely surrounded by Cas gets him. Dean lets loose a wail of Cas' name against the hand at his mouth as he comes, only barely having the presence of mind to make sure that he doesn't get come on his pants where they're pooled around his ankles. Seconds later he feels the collar of his shirt tugging at his throat and realizes that Cas has bitten down on the back of his collar to stifle his own groan as his hips stutter, and then the sensation of Cas' come spurting inside him.

Normally when Dean is shaky after sex it's due to sensory overload or tired muscles, but this time he knows better, the moment he feels Cas' forehead drop to rest on the top of his shoulder blade, and the hand on his mouth slip off. They stay quiet for a long minute, both men panting hard, even though Dean didn't really have to do more than just stand there. Cas raises his head and Dean feels the man tense so hard behind him, his dick nearly slips out, and he starts to pull his hand away.

Before he's really planned on it, Dean clenches both his fingers and his ass, trying to keep Cas from leaving. "Please, just…give me a minute?" Dean murmurs, hoping the quiet tone will hide the shakiness in his voice.

He hears Cas swallow harshly behind him, but then his forehead comes back down to Dean's shoulder, and Cas thrusts slowly, shallowly inside Dean with what's left of his waning erection. It's almost like Cas is trying to pet Dean's insides with his dick, and something about it just feels so affectionate that all those feelings-thoughts come rushing back ten fold. Shit. Cas didn't fuck the feelings out of him; no, the man fucked even more of them in, and Dean is struck with the sudden urge to laugh at his own stupidity.

Of course Dean had to go and develop fucking feelings. And what the hell did he expect, when he spends more time with Cas than anyone else, between work and play? The man makes sure he has his shit together at work, keeps him fed- since Dean takes the majority of his meals at work- and even knows all of Dean's dietary and personal food preferences, has a key to his apartment so he can get in if Dean forgets something he needs…shit. How in the hell did he not notice that they're practically in a relationship, even without the work thing?

He feels Cas pull out gently, but can't bring himself to stand up, even though his back would thank him for it. Wordlessly, Cas crouches down and pulls Dean's pants and underwear back up, and start to tuck his shirt back in, in the back. With a grunt, Dean finally rights himself, knowing that Cas doesn't do anything half-assed and will want to finish what he started; it'll be easier on him if Dean is upright. Instead of coming around Dean's front though, Cas leans in close to his back and reaches around to Dean's front to finish the job, tucking Dean's shirt in and then doing up the front of Dean's pants and re-latching his belt.

Once he's finished, Cas' hands rest on Dean's belt and there's a pause where neither of them seems inclined to move. They both know that this time was different, and seem to be trying to figure out what to do next with the revelation. Cas' fingers fiddle over the buckle for a moment, and then the man sighs, presses a kiss to Dean's shoulder blade so softly that Dean isn't sure if he imagined it, and then pulls away with a quiet clearing of his throat.

"I think we should talk after work," Cas says as Dean turns around. "When we can speak as equals."

Dean nods. "I have time to take my lunch right now, don't I?"

Cas glances at his watch. "Yes, I scheduled for seven minutes from now."

"Good. Will you um…will you stay with me for a few more minutes?" Dean asks, tilting his head toward the leather couch that's been there since before he got the office.

Cas gives him a soft smile. "Of course," he replies, and they sit down on the couch.

After a few seconds, Dean gives up on pretense and lies down on his side, putting his head in Cas' lap, relaxing when he feels those long fingers start scratching at the back of his head, where he doesn't bother with product. This is one of Dean's favorite ways to come down from a scene with Cas and despite the awkward tension, he still craves this intimate touch and is glad that Cas isn't withholding it from him. They don't speak for the next several minutes, until the soft 'bing' sounds from Dean's computer, reminding him of his lunch.

Dean begrudgingly sits back up, not quite done having his recovery period, but reminding himself that Cas is only going back to his desk and will be spending time with him later. It also helps that Cas runs a soothing palm over Dean's back for a moment, giving him a few last words of praise before standing up and exiting Dean's office. For the rest of the day they'll be in business-only mode, but as long as Dean knows Cas is around, it'll be okay.

Thankfully, Dean has plenty of work to keep him occupied and yet again keeping his thoughts mostly away from the anticipation he's come to associate with Cas, as well as the fact that his boxers are probably pretty well a mess of come and lube. This time though, it's a much different sort of anticipation that zings through him when he sends the last email of the day and realizes that this will be the first time that he and Cas will be meeting up outside of work for something besides a romp. As Dean gets his space shut down for the day, his nervousness ramps up and he's glad they decided to meet up to eat, rather than drive together because Dean is going to need the few minutes drive to the restaurant to get himself together.

Cas already poked his head in the door to confirm their plans and announce that he was heading out, so Dean can't really fiddle around because Cas will be waiting on him. He has no clue what direction Cas is going to take with the conversation, but Dean figures it could be anything from cutting off their extracurricular activity, to calling out Dean's feelings and letting him down gently.

As he pulls up to the restaurant, he realizes there really just isn't any good way to prepare and the thought of going in without a plan makes his pulse thump harshly. Dean Smith lives a life of to-the-minute itineraries, exact calories counted and balanced with exact miles jogged on the treadmill. He drops off his dry cleaning every Wednesday during his lunch, brushes his teeth for exactly two and a half minutes, and scrubs his stove on the first day of every month. Ridiculously, he even keeps an accordion folder full of greeting cards for every occasion, each in their own little labeled section, just in case he needs one at the last minute. So going into a personal meeting without a plan? This is miles out of Dean's comfort zone.

When he walks in and sees Cas already seated and with a glass of water with no ice and two lime wedges in a dish waiting for him though, Dean feels something settle in himself. Cas takes good care of him in every situation, so there's no reason to doubt that he will right now, too.

"Long time no see," Cas greets him with a wry smile as Dean approaches.

Dean's never heard anything remotely near a joke leave Cas' mouth and can't help but grin as he sits down. He's seen Cas laugh at things and even to himself, but never actually say something with much of a humorous lilt to it. Still though, Dean doesn't quite know how to respond, so he sets about squeezing his lime in his water and throws Cas a wink of acknowledgement. And because Cas is Cas, he knows exactly how nervous Dean is and stretches out a leg to hook their ankles together in a reassuring gesture. It goes farther to soothe him than Dean would like to admit.

After the server has taken their orders, Cas leans back and loosens his ties and the top button of his shirt and takes a deep, relieved breath before finally speaking.

"You know how I asked off for next Tuesday morning?" Cas asks.

"Yes?" Dean asks, drawing the word out.

"I have a job interview," Cas confesses, looking utterly sheepish. "The high school near my place is needing a history teacher, and well," he shrugs.

Dean blinks, processing the information. He knew when he hired Cas that the man had a history degree and a philosophy degree and assumed that the job market hadn't been offering up much for his qualifications. Not that it mattered to his current job; he could've had a degree in ribbon curling and gotten the job, what with his natural talent for organization. But it hadn't occurred to Dean that Cas would still be actively looking for something more appropriate to his educational background.

"That's uh…congrats, Cas," Dean says, forcing a grin to his face. And a piece of him really is happy for Cas, but a bigger piece of Dean is selfish and clingy and doesn't want Cas to go. Because if they aren't seeing each other everyday, then what's to keep Cas coming back to him after hours? "Sure sounds a sight better that waiting hand and foot on a suit in a corporate office everyday."

Cas' expression softens and he lays a hesitant hand over Dean's where it's resting on the table. When Dean doesn't pull it away, Cas curls his fingers around Dean's palm and brushes his thumb over the back of Dean's hand.

"Dean, I don't mind my job. But it also isn't what I really wanted to do. And I've hit a bit of a snag, you see. Because I've kind of um," Cas pauses and swallows nervously. "I might have also developed some inappropriate feelings for my boss."

Dean blinks at Cas, trying to process what he just heard. So…it's actually the opposite of the rejection Dean had been expecting. Holy shit. God, he wants to yank Cas across the table and kiss him senseless, but unfortunately, that's nowhere near what happens.

"No offense Cas, but I don't think you're ole' Zachariah's type," Dean says, earning an irritated frown.

"And this is why I didn't say anything about leaving," Cas mutters, pulling his hand away.

Dean would love nothing more than to punch himself in the face a la Tyler Durden for saying such a stupid, insensitive thing just because he's not always sure how to react. When he was a kid he was mocked for being too sensitive, and as a younger man being too insensitive, and as a fully grown man, he still rides a line between still being all soft and gooey on the inside, and trying to restrain himself from letting too much of it out, on the outside. And now Cas is looking about six shades of mortified and rejected, and it's Dean's fault.

Dragging a hand down his face, Dean groans. "I don't know why I said that, and I'm really sorry, Cas. If it makes a difference, I'm kind of going through the same thing with my secretary," he confesses.

Cas gives him a long look, and after several seconds, something resembling hope starts to creep into his eyes.

"You said it because you have a kind heart that hasn't always been treated well, and you're always waiting for the other shoe to drop," Cas says, voice soft again.

Dean feels his face twitch, trying to settle on what emotion to show when he doesn't even know how to feel about that, himself. Fortunately, Cas seems to understand and doesn't seem to expect a response, moving on to address the second part of what Dean said.

"I don't have any 'buts' to offer, no shoe. There are just so many more ways than what our situation permits that I would like to be able to spend time with you or touch you. And I understand if this makes you uncomfortable; I'll quit tomorrow if you don't want to see me again, but I just needed you to know," Cas finishes quietly.

Dean's pretty sure his heart is going to pop out of his chest with how wildly it's beating. Cas wants him back. And if that interview goes well, they can actually have something instead of ducking and hiding and pretending it's just sex; rather unethical but scorchingly hot sex that would undoubtedly get both of them fired, but still. All those fuzzy gooey sappy things that Dean wouldn't dare ask for are being implicitly offered right here in front of him, and yet again the battle for restraint wages on. So maybe his next words are a copout, to get to have the experience of getting those words out, risk-free in a way.

"Tell me what we'd be doing tonight if we were together," Dean says, a tentative smile tugging at his lips.

Cas quirks an amused brow, but humors Dean all the same.

"We'd have a relaxing dinner, then go home and lay around on the couch in our underwear, or maybe take a bath so you can take care of the mess I made of your ass earlier. Make out for a while; maybe we get off, maybe we don't," Cas shrugs with a little grin. "I'd make a cup of tea and crawl up in the bed and read a couple chapters on the book I'm reading, and then when my tea hits me, curl up and go to sleep with you."

"Wow…that's…shockingly vanilla," Dean chuckles.

"It's a Wednesday, and we aren't twenty anymore. What do you expect?" Cas asks lightly.

"Not complaining or making fun, I'm just surprised," Dean explains. "It actually sounds really nice."

Cas taps the side of his own water glass for a moment. "Wanna give it a test drive?" he asks, a shy little smile pulling at his lips.

"Do I get to put the key in the ignition?" Dean asks with a lewd smirk. But he really does kind of want to know.

"Maybe if you promise not to allude to anal sex as turning me on and cranking my engine again," Cas replies smoothly.

Dean snorts a laugh. "Okay, okay. I know that was a bad innuendo."

"The worst, Mr. Smith," Cas agrees with a straight face that doesn't match the humor twinkling in his eye.

And just like that, Dean is swallowing hard because if Cas gets that teaching job…oh god…

"I knew you had a thing for that," Cas smirks. "What's that about, anyway?" he asks curiously.

Dean shakes his head, a blush working its way up his neck. Cas eyes him speculatively, head tilted as his eyes narrow in thought.

"It's not an enjoyment of title," Cas muses aloud. "And I doubt it's about having that bit of authority over me at work," he says, rubbing a hand along his jaw.

But then Cas' eyes widen in tentative excitement and leans forward to speak more softly. "Tell me, _Mr. Smith_ , have you been _bad_ and talking when the teacher said to stay quiet?" he asks, mustering up that deep gravel that makes Dean's toes curl. Then, with a thoughtful look, Cas reaches forward and hooks an index finger around one of Dean's suspenders and pulls back. Oh no. Nononono-

_Snap!_

Right on the nipple, oh Jesus fuck, he should not have enjoyed that.

His face has to be on fire, and it's not helped at all when Cas lets loose a dark chuckle at the very visible blush. Then that finger is hooking right around the suspender again.

"I asked you a question," Cas smirks, toying with the elastic in his hand.

"Y-yes Sir. I was much too loud when I shouldn't have been," Dean says, blinking innocently.

Somehow Cas looks just as amused as he does aroused, and slowly releases the suspender back to its resting place.

"I thought as much. That's ten snaps for you, to be delivered tomorrow at my discretion," Cas says seriously, but yet again, there's that twinkle.

That twinkle will be the death of him.

**Author's Note:**

> My [Tumblr](http://surly-cat.tumblr.com) if you wanna stop by and have feelings or share porny thoughts with me ;)


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